(Z)-1-methoxy-5,5-bis(methoxymethyl)non-2-en-7-yne | 844821-28-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-methoxy-5,5-bis(methoxymethyl)non-2-en-7-yne
• 英文别名: (2Z)-1-Methoxy-5,5-bis(methoxymethyl)-2-nonen-7-yne
• CAS: 844821-28-9
• 化学式: C₁₄H₂₄O₃
• 分子量: 240.343
• InChiKey: RZUILXVNKJCFGD-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯硼酸 、 (Z)-1-methoxy-5,5-bis(methoxymethyl)non-2-en-7-yne 在 [Rh(OH)(cod)]2 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以81%的产率得到(Z)-1,1-bis(methoxymethyl)-3-(1-phenylethylidene)-4-vinylcyclopentane
  参考文献：
  名称：

  Rhodium-Catalyzed Cyclization of 1,6-Enynes Triggered by Addition of Arylboronic Acids

  摘要：

  1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by beta-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.

  DOI：

  10.1021/ja0435079

文献信息

• Rhodium-Catalyzed Cyclization of 1,6-Enynes Triggered by Addition of Arylboronic Acids
  作者：Tomoya Miura、Masahiko Shimada、Masahiro Murakami

  DOI：10.1021/ja0435079

  日期：2005.2.1

  1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by beta-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.